We would buy this house all cash. 

The thing to remember also is that I buy super duper priced houses.

@Connor ChatlosDenver and Chicago's high property values make multifamily properties ideal for house hacking.

I'm a house hacker too, message me if you want to connect 

Do you plan on renting out your current house or house hacking it? 

I always am amazed when someone selling a $600,000 house brings me a listing agreement where they agreed to pay a stranger $30,000 to list their house for sale and they didn't even read the agreement much less spend the $250 to have a lawyer tell them that yes, if they sell it to their cousin during the listing period they still have to pay the $30k.

He will get around $3,100 tax free Base housing allowance and will have $150,000 he can put down.  

If house hacking isn't the best option for me, how would you recommend starting out to build up some investments.

Quote from @Jenny Banner: Good Afternoon,I have flipped a few houses up in Connecticut.

For example, if a seller comes to you, looking for you to help them sell their house, your first responsibility is to help them get the most money for their house, and not try to buy their house as an investor for cheaper.